1559r.ch21.373-38810/18/0518:42Page38g 388.chapter 21 AMINES AND THEIR DERIVATIVES:FUNCTIONAL GROUPS CONTAINING NITROGEN (b)The ionic salt NaCN is essentially insoluble in decane.Thus the concentration of nucleophilic cyanide ion in solution is exceedingly tiny,and S2 reaction is correspondingly slow. (e)The ammonium cation may exchange counterions (cyanide for chloride)when it is in the water layer,and upon transfer to the decane. ide may acco an a significant 57.(c) 58.@ 59.e) 60.(a 61.(dThe electrophilic substitution is in fact another variation of the Mannich reaction as well, with the electron-rich benzene ring acting as the nucleophile. 56. (a) The catalyst, being a salt, should have some solubility in the water. Because it contains several hydrocarbon substituents on nitrogen, it should also possess some solubility in decane as well. (b) The ionic salt NaCN is essentially insoluble in decane. Thus the concentration of nucleophilic cyanide ion in solution is exceedingly tiny, and SN2 reaction is correspondingly slow. (c) The ammonium cation may exchange counterions (cyanide for chloride) when it is in the water layer, and upon transfer to the decane, cyanide may accompany it. Thus, a significant concentration of cyanide may develop in the decane to participate in SN2 reaction with the chlorooctane. 57. (c) 58. (c) 59. (e) 60. (a) 61. (d) 388 • Chapter 21 AMINES AND THEIR DERIVATIVES: FUNCTIONAL GROUPS CONTAINING NITROGEN 1559T_ch21_373-388 10/18/05 18:42 Page 388